JP6438947B2 - 有機化合物 - Google Patents
有機化合物 Download PDFInfo
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- JP6438947B2 JP6438947B2 JP2016522536A JP2016522536A JP6438947B2 JP 6438947 B2 JP6438947 B2 JP 6438947B2 JP 2016522536 A JP2016522536 A JP 2016522536A JP 2016522536 A JP2016522536 A JP 2016522536A JP 6438947 B2 JP6438947 B2 JP 6438947B2
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- Prior art keywords
- mmol
- phenyl
- methyl
- nmr
- cdcl
- Prior art date
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- 150000002894 organic compounds Chemical class 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims description 96
- 150000001875 compounds Chemical class 0.000 claims description 37
- 239000003205 fragrance Substances 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 28
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 18
- -1 propen-2-yl Chemical group 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- BMCWFGPRVVKAAC-UHFFFAOYSA-N CC(C)CCCc1cccc(c1)C(C)CC=O Chemical compound CC(C)CCCc1cccc(c1)C(C)CC=O BMCWFGPRVVKAAC-UHFFFAOYSA-N 0.000 claims description 7
- VEABUJASOCQMFM-UHFFFAOYSA-N CC(C)CCc1cccc(c1)C(C)CC=O Chemical compound CC(C)CCc1cccc(c1)C(C)CC=O VEABUJASOCQMFM-UHFFFAOYSA-N 0.000 claims description 7
- OPHSGYDJCHDYAG-UHFFFAOYSA-N CC(Cc1cccc(CCC(C)=C)c1)C=O Chemical compound CC(Cc1cccc(CCC(C)=C)c1)C=O OPHSGYDJCHDYAG-UHFFFAOYSA-N 0.000 claims description 7
- PXKYIPVGPBVGRO-UHFFFAOYSA-N CC(C)CCc1cccc(CC(C)C=O)c1 Chemical compound CC(C)CCc1cccc(CC(C)C=O)c1 PXKYIPVGPBVGRO-UHFFFAOYSA-N 0.000 claims description 6
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 5
- ZCDRBAQCSBNJOR-UHFFFAOYSA-N CC(C=O)C(C)c1cccc(CCC(C)=C)c1 Chemical compound CC(C=O)C(C)c1cccc(CCC(C)=C)c1 ZCDRBAQCSBNJOR-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- YRKWOYHYNUHUSL-UHFFFAOYSA-N CC(Cc1cccc(CCC2CC2)c1)C=O Chemical compound CC(Cc1cccc(CCC2CC2)c1)C=O YRKWOYHYNUHUSL-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000000047 product Substances 0.000 description 45
- 239000000243 solution Substances 0.000 description 32
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 31
- 235000019645 odor Nutrition 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 26
- 238000003756 stirring Methods 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 16
- 239000007788 liquid Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 10
- 239000002537 cosmetic Substances 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- 239000005457 ice water Substances 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000003818 flash chromatography Methods 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 238000000023 Kugelrohr distillation Methods 0.000 description 7
- 239000012300 argon atmosphere Substances 0.000 description 7
- 239000012298 atmosphere Substances 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000002304 perfume Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000002198 insoluble material Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- SUISZCALMBHJQX-UHFFFAOYSA-N 3-bromobenzaldehyde Chemical compound BrC1=CC=CC(C=O)=C1 SUISZCALMBHJQX-UHFFFAOYSA-N 0.000 description 4
- JLXQSHYFGIBTPI-UHFFFAOYSA-N CC(C)(O)CCc1cccc(C=O)c1 Chemical compound CC(C)(O)CCc1cccc(C=O)c1 JLXQSHYFGIBTPI-UHFFFAOYSA-N 0.000 description 4
- 244000068485 Convallaria majalis Species 0.000 description 4
- 235000009046 Convallaria majalis Nutrition 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000006383 Hayashi-Miyaura coupling reaction Methods 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 239000000341 volatile oil Substances 0.000 description 3
- VYXHVRARDIDEHS-QGTKBVGQSA-N (1z,5z)-cycloocta-1,5-diene Chemical compound C\1C\C=C/CC\C=C/1 VYXHVRARDIDEHS-QGTKBVGQSA-N 0.000 description 2
- FOHUDAFFAVYJHU-FMIVXFBMSA-N (E)-3-[3-(3-hydroxy-3-methylbutyl)phenyl]-2-methylprop-2-enal Chemical compound OC(CCC=1C=C(C=CC=1)/C=C(/C=O)\C)(C)C FOHUDAFFAVYJHU-FMIVXFBMSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OPNDWUNGMWNXNB-UHFFFAOYSA-N 1,5-benzodioxepin-3-one Chemical class O1CC(=O)COC2=CC=CC=C21 OPNDWUNGMWNXNB-UHFFFAOYSA-N 0.000 description 2
- VERUENJPKLDCKE-UHFFFAOYSA-N 1-(3-bromophenyl)-4-methylpentan-1-ol Chemical compound CC(C)CCC(O)C1=CC=CC(Br)=C1 VERUENJPKLDCKE-UHFFFAOYSA-N 0.000 description 2
- NNUWHKZHDXKRMU-UHFFFAOYSA-N 1-chloro-3-(3-methylbut-3-enyl)benzene Chemical compound CC(=C)CCC1=CC=CC(Cl)=C1 NNUWHKZHDXKRMU-UHFFFAOYSA-N 0.000 description 2
- BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 2
- UDKPLWDQSJVECZ-QPJJXVBHSA-N 3-[3-[(E)-4-methylpent-1-enyl]phenyl]butanal Chemical compound CC(C/C=C/C=1C=C(C=CC=1)C(CC=O)C)C UDKPLWDQSJVECZ-QPJJXVBHSA-N 0.000 description 2
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical class O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 2
- ORMHZBNNECIKOH-UHFFFAOYSA-N 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde Chemical compound CC(C)(O)CCCC1=CCC(C=O)CC1 ORMHZBNNECIKOH-UHFFFAOYSA-N 0.000 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XBQWMWGFGMXVAH-UHFFFAOYSA-N CC(=C)CCc1cccc(c1)B(O)O Chemical compound CC(=C)CCc1cccc(c1)B(O)O XBQWMWGFGMXVAH-UHFFFAOYSA-N 0.000 description 2
- BMCWFGPRVVKAAC-AWEZNQCLSA-N CC(C)CCCc1cccc(c1)[C@@H](C)CC=O Chemical compound CC(C)CCCc1cccc(c1)[C@@H](C)CC=O BMCWFGPRVVKAAC-AWEZNQCLSA-N 0.000 description 2
- BMCWFGPRVVKAAC-CQSZACIVSA-N CC(C)CCCc1cccc(c1)[C@H](C)CC=O Chemical compound CC(C)CCCc1cccc(c1)[C@H](C)CC=O BMCWFGPRVVKAAC-CQSZACIVSA-N 0.000 description 2
- VWYBQRRMQKYRLL-FPLPWBNLSA-N CC(C)\C=C/c1cccc(C(C)CC=O)c1 Chemical compound CC(C)\C=C/c1cccc(C(C)CC=O)c1 VWYBQRRMQKYRLL-FPLPWBNLSA-N 0.000 description 2
- CHTBJZBIJSJUSQ-UHFFFAOYSA-N CC(CC=O)c1cccc(CCC2CC2)c1 Chemical compound CC(CC=O)c1cccc(CCC2CC2)c1 CHTBJZBIJSJUSQ-UHFFFAOYSA-N 0.000 description 2
- 241000207199 Citrus Species 0.000 description 2
- 244000241257 Cucumis melo Species 0.000 description 2
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 2
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 150000001543 aryl boronic acids Chemical class 0.000 description 2
- 238000011914 asymmetric synthesis Methods 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 2
- HQKQRXZEXPXXIG-VJOHVRBBSA-N chembl2333940 Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@H]1[C@@](OC(C)=O)(C)CC2 HQKQRXZEXPXXIG-VJOHVRBBSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- 235000020971 citrus fruits Nutrition 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 2
- WCASXYBKJHWFMY-UHFFFAOYSA-N crotyl alcohol Chemical compound CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 150000002678 macrocyclic compounds Chemical class 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000035807 sensation Effects 0.000 description 2
- 235000019615 sensations Nutrition 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000001069 triethyl citrate Substances 0.000 description 2
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 2
- 235000013769 triethyl citrate Nutrition 0.000 description 2
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 2
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- ORHSGDMSYGKJJY-SAIIYOCFSA-N (1'r,6's)-2,2,4',7',7'-pentamethylspiro[1,3-dioxane-5,5'-bicyclo[4.1.0]heptane] Chemical compound C12([C@H]3[C@H](C3(C)C)CCC2C)COC(C)(C)OC1 ORHSGDMSYGKJJY-SAIIYOCFSA-N 0.000 description 1
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 description 1
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 description 1
- AVJMJMPVWWWELJ-DHZHZOJOSA-N (2e)-1-methoxy-3,7-dimethylocta-2,6-diene Chemical compound COC\C=C(/C)CCC=C(C)C AVJMJMPVWWWELJ-DHZHZOJOSA-N 0.000 description 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- DCSCXTJOXBUFGB-MQWKRIRWSA-N (5r)-2,6,6-trimethylbicyclo[3.1.1]hept-2-en-4-one Chemical compound CC1=CC(=O)[C@H]2C(C)(C)C1C2 DCSCXTJOXBUFGB-MQWKRIRWSA-N 0.000 description 1
- NEJDKFPXHQRVMV-UHFFFAOYSA-N (E)-2-Methyl-2-buten-1-ol Natural products CC=C(C)CO NEJDKFPXHQRVMV-UHFFFAOYSA-N 0.000 description 1
- NVIPUOMWGQAOIT-UHFFFAOYSA-N (E)-7-Hexadecen-16-olide Natural products O=C1CCCCCC=CCCCCCCCCO1 NVIPUOMWGQAOIT-UHFFFAOYSA-N 0.000 description 1
- XTHUGLFFHZPVGL-XQHVRGAUSA-N (E)-but-2-en-1-ol Chemical compound C(\C=C\C)O.C(\C=C\C)O XTHUGLFFHZPVGL-XQHVRGAUSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
- C07C47/105—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing rings
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- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
- C07C47/105—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing rings
- C07C47/11—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing rings monocyclic
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- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
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- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
- C07C47/232—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde having unsaturation outside the aromatic rings
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- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/235—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- Chemical & Material Sciences (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| PCT/CN2013/078376 WO2014205782A1 (en) | 2013-06-28 | 2013-06-28 | Organic compounds |
| CNPCT/CN2013/078376 | 2013-06-28 | ||
| PCT/EP2014/063699 WO2014207205A1 (en) | 2013-06-28 | 2014-06-27 | Organic compounds |
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| Publication Number | Publication Date |
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| JP2016530227A JP2016530227A (ja) | 2016-09-29 |
| JP2016530227A5 JP2016530227A5 (enrdf_load_stackoverflow) | 2017-08-03 |
| JP6438947B2 true JP6438947B2 (ja) | 2018-12-19 |
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| US (1) | US9708570B2 (enrdf_load_stackoverflow) |
| EP (1) | EP3013782B1 (enrdf_load_stackoverflow) |
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| WO (2) | WO2014205782A1 (enrdf_load_stackoverflow) |
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| WO2017009175A1 (en) * | 2015-07-14 | 2017-01-19 | Firmenich Sa | Compound having a muguet odor |
| EP3571273B1 (en) | 2017-01-18 | 2020-09-23 | Firmenich SA | Composition having a muguet odor |
| CN110177861B (zh) * | 2017-01-18 | 2023-07-28 | 弗门尼舍有限公司 | 具有铃兰气味的组合物 |
| US12116338B2 (en) | 2019-10-17 | 2024-10-15 | Mitsubishi Gas Chemical Company, Inc. | Aldehyde compound and method for producing same, and fragrance composition |
| EP4314216A1 (en) * | 2021-04-01 | 2024-02-07 | Basf Se | 2-(2-(3-methylbut-2-en-1yl)phenyl) propanal and mixtures thereof as aroma ingredient |
| CN114133982B (zh) * | 2021-11-23 | 2024-02-27 | 万华化学集团股份有限公司 | 一种制备具有玫瑰香味的香料的方法及组合物原料 |
| JP7552961B2 (ja) | 2022-06-17 | 2024-09-18 | 三菱瓦斯化学株式会社 | アルデヒド組成物 |
Family Cites Families (23)
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| FR1364620A (fr) | 1963-03-15 | 1964-06-26 | Rhone Poulenc Sa | Aldéhyde p. isobutyldihydrocinnamique |
| US3548006A (en) | 1963-03-15 | 1970-12-15 | Rhone Poulenc Sa | Aldehydes useful in perfumery |
| BE672280A (enrdf_load_stackoverflow) * | 1964-11-13 | 1966-05-12 | ||
| GB2079751B (en) * | 1980-07-09 | 1985-02-06 | Albright & Wilson | Process for the production of alkyl-phenyl propanals and some products thereof |
| JPH03221599A (ja) | 1990-01-26 | 1991-09-30 | Takasago Internatl Corp | 香料組成物 |
| US5095152A (en) | 1990-11-21 | 1992-03-10 | Union Camp Corporation | Novel heptamethyl indane compound |
| EP0652861B1 (fr) | 1993-05-26 | 1997-09-03 | Firmenich Sa | Composes aromatiques nouveaux et leur utilisation en parfumerie |
| DE69516036T2 (de) | 1994-05-31 | 2000-12-21 | Firmenich S.A., Genf/Geneve | Aromatische Verbindungen und ihre Verwendung in der Parfümerie |
| US6465410B1 (en) | 1999-04-30 | 2002-10-15 | The Procter & Gamble | Laundry detergent and/or fabric care composition comprising a modified antimicrobial protein |
| US6342612B1 (en) | 2001-01-26 | 2002-01-29 | International Flavors & Fragrances Inc. | Indane aldehydes and derivatives |
| US8188126B2 (en) | 2002-05-16 | 2012-05-29 | Pierre Fabre Medicament | Imidazolic compounds and use thereof as alpha-2 adrenergic receptors |
| DE602007012072D1 (de) | 2006-04-26 | 2011-03-03 | Actelion Pharmaceuticals Ltd | Orantagonisten |
| US7652053B2 (en) | 2006-11-30 | 2010-01-26 | Hoffmann-La Roche Inc. | Diaminocycloalkane MCH receptor antagonists |
| US8754028B2 (en) | 2008-12-16 | 2014-06-17 | The Procter & Gamble Company | Perfume systems |
| WO2010091969A1 (en) * | 2009-02-13 | 2010-08-19 | Basf Se | Lily of the valley-type fragrance compositions |
| DE102009001569A1 (de) | 2009-03-16 | 2010-09-23 | Henkel Ag & Co. Kgaa | Lilial-Substitut |
| ES2487217T3 (es) * | 2009-10-23 | 2014-08-20 | Basf Se | Procedimiento para la preparación de fenilalcanoles m-sustituidos mediante isomerización |
| TW201238603A (en) * | 2011-03-10 | 2012-10-01 | Lonza Ag | Method for preparation of 3-(2,3-dimethylphenyl)-2-butenal |
| CN103874755B (zh) | 2011-09-30 | 2016-08-17 | 弗门尼舍有限公司 | 花香加香组合物 |
| US8999990B2 (en) | 2011-10-25 | 2015-04-07 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| WO2012172122A2 (en) | 2012-06-28 | 2012-12-20 | Lonza Ltd | Method for the preparation of 2-(2,3-dimethylphenyl)-1-propanal |
| GB201308248D0 (en) | 2013-05-08 | 2013-06-12 | Givaudan Sa | Improvements in or relating to organic compounds |
| GB201308236D0 (en) | 2013-05-08 | 2013-06-12 | Givaudan Sa | Improvements in or relating to organic compounds |
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- 2014-06-27 EP EP14733640.8A patent/EP3013782B1/en active Active
- 2014-06-27 WO PCT/EP2014/063699 patent/WO2014207205A1/en active Application Filing
- 2014-06-27 JP JP2016522536A patent/JP6438947B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP3013782A1 (en) | 2016-05-04 |
| WO2014207205A1 (en) | 2014-12-31 |
| JP2016530227A (ja) | 2016-09-29 |
| WO2014205782A1 (en) | 2014-12-31 |
| US20160369205A1 (en) | 2016-12-22 |
| EP3013782B1 (en) | 2018-10-03 |
| US9708570B2 (en) | 2017-07-18 |
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